US7629461B2 - Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard - Google Patents

Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard Download PDF

Info

Publication number: US7629461B2
Authority: US; United States
Prior art keywords: valacyclovir; formyl; sample; hplc; reaction mixture
Prior art date: 2004-09-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related, expires 2026-06-18

Application number

US11/221,124

Other languages

English (en)

Other versions

US20060084668A1 (en

Inventor

Amihai Eisenstadt

Michael Pesachovich

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Teva Pharmaceutical Industries Ltd

Teva Pharmaceuticals USA Inc

Original Assignee

Teva Pharmaceutical Industries Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-09-04

Filing date

2005-09-06

Publication date

2009-12-08

2005-09-06 Application filed by Teva Pharmaceutical Industries Ltd filed Critical Teva Pharmaceutical Industries Ltd

2005-09-06 Priority to US11/221,124 priority Critical patent/US7629461B2/en

2005-12-29 Assigned to TEVE PHARMACEUTICAL INDUSTRIES LTD. reassignment TEVE PHARMACEUTICAL INDUSTRIES LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PESACHOVICH, MICHAEL, EISENSTADT, AMIHAI

2005-12-29 Assigned to TEVA PHARMACEUTICALS USA, INC. reassignment TEVA PHARMACEUTICALS USA, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TEVA PHARMACEUTICAL INDUSTRIES LTD.

2006-04-20 Publication of US20060084668A1 publication Critical patent/US20060084668A1/en

2006-09-05 Assigned to TEVA PHARMACEUTICAL INDUSTRIES LTD. reassignment TEVA PHARMACEUTICAL INDUSTRIES LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PESACHOVICH, MICHAEL, EISENSTADT, AMIHAI

2009-12-08 Application granted granted Critical

2009-12-08 Publication of US7629461B2 publication Critical patent/US7629461B2/en

Status Expired - Fee Related legal-status Critical Current

2026-06-18 Adjusted expiration legal-status Critical

Links

HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 title claims description 86
229940093257 valacyclovir Drugs 0.000 title claims description 82
238000000034 method Methods 0.000 title claims description 42
239000012535 impurity Substances 0.000 title claims description 39
238000002360 preparation method Methods 0.000 title abstract description 10
AYGHYIMPMGWQND-VIFPVBQESA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl (2s)-2-formamido-3-methylbutanoate Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](NC=O)C(C)C)C=N2 AYGHYIMPMGWQND-VIFPVBQESA-N 0.000 claims abstract description 76
238000004128 high performance liquid chromatography Methods 0.000 claims description 38
239000011541 reaction mixture Substances 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 5
230000035484 reaction time Effects 0.000 claims description 4
238000001816 cooling Methods 0.000 claims description 3
238000005259 measurement Methods 0.000 claims description 2
239000003550 marker Substances 0.000 abstract description 26
150000001875 compounds Chemical class 0.000 description 23
239000008186 active pharmaceutical agent Substances 0.000 description 22
239000000523 sample Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 20
239000000243 solution Substances 0.000 description 14
230000014759 maintenance of location Effects 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 10
238000001514 detection method Methods 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
238000004451 qualitative analysis Methods 0.000 description 8
238000011002 quantification Methods 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000003480 eluent Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000004445 quantitative analysis Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000004458 analytical method Methods 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000012086 standard solution Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229960004150 aciclovir Drugs 0.000 description 3
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000012088 reference solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
-1 L-valyl ester Chemical class 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
YJAWHJDEDHTPPH-PVSSEACSSA-N N.O.[H][C@@](N)(C(=O)OCCOCN1C=NC2=C(O)N=C(N)N=C21)C(C)C.[H][C@@](NC=O)(C(=O)OCCOCN1C=NC2=C(O)N=C(N)N=C21)C(C)C Chemical compound N.O.[H][C@@](N)(C(=O)OCCOCN1C=NC2=C(O)N=C(N)N=C21)C(C)C.[H][C@@](NC=O)(C(=O)OCCOCN1C=NC2=C(O)N=C(N)N=C21)C(C)C YJAWHJDEDHTPPH-PVSSEACSSA-N 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000010954 commercial manufacturing process Methods 0.000 description 2
239000007857 degradation product Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000011491 glass wool Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000003760 magnetic stirring Methods 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000013074 reference sample Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000012488 sample solution Substances 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
229940108442 valtrex Drugs 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
238000012573 2D experiment Methods 0.000 description 1
HDOVUKNUBWVHOX-UHFFFAOYSA-N CC(C)C(N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O Chemical compound CC(C)C(N)C(=O)OCCOCN1C=NC2=C1NC(N)=NC2=O HDOVUKNUBWVHOX-UHFFFAOYSA-N 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
241000700605 Viruses Species 0.000 description 1
WTAKOYJWYYIQOL-GFCCVEGCSA-N [H][C@](NC=O)(C(=O)OCCOCN1C=NC2=C1NC(N)=CC2=O)C(C)C Chemical compound [H][C@](NC=O)(C(=O)OCCOCN1C=NC2=C1NC(N)=CC2=O)C(C)C WTAKOYJWYYIQOL-GFCCVEGCSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000007905 drug manufacturing Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
238000012856 packing Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001448 refractive index detection Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000012827 research and development Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000000357 thermal conductivity detection Methods 0.000 description 1
238000011282 treatment Methods 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
239000004474 valine Substances 0.000 description 1
230000009385 viral infection Effects 0.000 description 1

Images

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
- Y10T436/147777—Plural nitrogen in the same ring [e.g., barbituates, creatinine, etc.]

Definitions

the term “reference standard” refers to a compound that may be used both for quantitative and qualitative analysis of an active pharmaceutical ingredient.
the HPLC retention time of the compound allows a relative retention time to be determined, thus making qualitative analysis possible.
the concentration of the compound in solution before injection into an HPLC (or GC) column allows the areas under the HPLC (or GC) peaks to be compared, thus making quantitative analysis possible.
a detector response can be, for example, the peak heights or integrated peak areas of a chromatogram obtained, e.g., by UV or refractive index detection, from the eluent of an HPLC system or, e.g., flame ionization detection (FID) or thermal conductivity detection, from the eluent of a gas chromatograph, or other detector response, e.g., the UV absorbance of spots on a fluorescent TLC plate.
the position of the reference standard may be used to calculate the relative retention time for valacyclovir and impurities of valacyclovir.
N-formyl valacyclovir although mentioned in the NDA for valacyclovir (Valtrex®), has never been obtained in substantially pure form, isolated from (that is separate and apart from) valacyclovir. To the best of Applicants' knowledge, the structure of N-formyl valacyclovir has never been discovered before (the location of N-formyl group being unknown).
the present invention provides a process for preparing a pharmaceutical composition comprising valacyclovir or a pharmaceutically acceptable salt thereof which comprises formulating valacyclovir or a pharmaceutically acceptable salt, tested according to any of the methods, which are part of this invention, above with an excipient of carrier.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Sampling And Sample Adjustment (AREA)
Analysing Materials By The Use Of Radiation (AREA)

US11/221,124 2004-09-04 2005-09-06 Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard Expired - Fee Related US7629461B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US11/221,124 US7629461B2 (en)	2004-09-04	2005-09-06	Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US60727904P	2004-09-04	2004-09-04
US11/221,124 US7629461B2 (en)	2004-09-04	2005-09-06	Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard

Publications (2)

Publication Number	Publication Date
US20060084668A1 US20060084668A1 (en)	2006-04-20
US7629461B2 true US7629461B2 (en)	2009-12-08

Family

ID=35734404

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US11/221,124 Expired - Fee Related US7629461B2 (en)	2004-09-04	2005-09-06	Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard

Country Status (8)

Country	Link
US (1)	US7629461B2 (fr)
EP (1)	EP1692134A2 (fr)
JP (1)	JP2007513074A (fr)
KR (1)	KR100890595B1 (fr)
CN (1)	CN101068814A (fr)
CA (1)	CA2578750A1 (fr)
IL (1)	IL181548A0 (fr)
WO (1)	WO2006029253A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20170052157A1 (en) *	2011-06-01	2017-02-23	Tsumura & Co.	Method of and apparatus for formulating multicomponent drug
RU2750867C1 (ru) *	2020-05-18	2021-07-05	Александр Сергеевич Самойлов	Производные гуанина

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EP2189456A1 (fr) *	2008-11-14	2010-05-26	LEK Pharmaceuticals d.d.	Nouveaux composés préparés à partir d'oméprazole
TW201613859A (en) *	2014-06-30	2016-04-16	Teva Pharma	Analogs of PRIDOPIDINE, their preparation and use
CN108037205A (zh) *	2017-12-20	2018-05-15	宜昌天仁药业有限责任公司	一种高效液相色谱测定cbz-伐昔洛韦含量的方法
CN110940754B (zh) *	2019-12-18	2022-08-12	湖北省宏源药业科技股份有限公司	一种分离测定盐酸伐昔洛韦中杂质的高效液相色谱方法
CN111879868A (zh) *	2020-06-30	2020-11-03	辰欣药业股份有限公司	一种盐酸伐昔洛韦有关物质的测定方法
CN115745997A (zh) *	2022-11-30	2023-03-07	湖北省宏源药业科技股份有限公司	一种高纯度伐昔洛韦杂质h制备方法

Citations (9)

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Publication number	Priority date	Publication date	Assignee	Title
US4957924A (en) *	1987-08-15	1990-09-18	Burroughs Wellcome Co.	Therapeutic valine esters of acyclovir and pharmaceutically acceptable salts thereof
WO1997027197A1 (fr)	1996-01-26	1997-07-31	F. Hoffmann-La Roche Ag	Procede pour la preparation de derives du ganciclovir
WO1998003553A1 (fr)	1996-07-18	1998-01-29	Industriale Chimica S.R.L.	Procede de preparation de valacyclovir et de produits intermediaires presentant un interet particulier
US6333198B1 (en)	1998-06-10	2001-12-25	Glaxo Wellcome, Inc.	Compound and its use
WO2003041647A2 (fr)	2001-11-14	2003-05-22	Teva Pharmaceutical Industries Ltd.	Synthese et purification de valacyclovir
US20050059684A1 (en)	2002-10-16	2005-03-17	Ben-Zion Dolitzky	Method for reducing residual alcohols in crystalline valacyclovir hydrochloride
US20050070711A1 (en) *	2002-10-16	2005-03-31	Igor Lifshitz	Method for reducing residual alcohols in crystalline valacyclovir hydrochloride
US20050143400A1 (en) *	2003-09-04	2005-06-30	Genny Shamai	Process for preparing famciclovir
US20070112193A1 (en) *	2005-11-14	2007-05-17	Khunt Mayur D	Valacyclovir process

2005
- 2005-09-06 CN CNA2005800294555A patent/CN101068814A/zh active Pending
- 2005-09-06 KR KR1020077006850A patent/KR100890595B1/ko not_active Expired - Fee Related
- 2005-09-06 JP JP2006538572A patent/JP2007513074A/ja active Pending
- 2005-09-06 EP EP05798745A patent/EP1692134A2/fr not_active Withdrawn
- 2005-09-06 US US11/221,124 patent/US7629461B2/en not_active Expired - Fee Related
- 2005-09-06 WO PCT/US2005/031952 patent/WO2006029253A2/fr not_active Ceased
- 2005-09-06 CA CA002578750A patent/CA2578750A1/fr not_active Abandoned
2007
- 2007-02-26 IL IL181548A patent/IL181548A0/en unknown

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4957924A (en) *	1987-08-15	1990-09-18	Burroughs Wellcome Co.	Therapeutic valine esters of acyclovir and pharmaceutically acceptable salts thereof
WO1997027197A1 (fr)	1996-01-26	1997-07-31	F. Hoffmann-La Roche Ag	Procede pour la preparation de derives du ganciclovir
WO1998003553A1 (fr)	1996-07-18	1998-01-29	Industriale Chimica S.R.L.	Procede de preparation de valacyclovir et de produits intermediaires presentant un interet particulier
US6333198B1 (en)	1998-06-10	2001-12-25	Glaxo Wellcome, Inc.	Compound and its use
WO2003041647A2 (fr)	2001-11-14	2003-05-22	Teva Pharmaceutical Industries Ltd.	Synthese et purification de valacyclovir
US20030153757A1 (en)	2001-11-14	2003-08-14	Etinger Marina Yu	Synthesis and purification of valacyclovir
US20050059684A1 (en)	2002-10-16	2005-03-17	Ben-Zion Dolitzky	Method for reducing residual alcohols in crystalline valacyclovir hydrochloride
US20050070711A1 (en) *	2002-10-16	2005-03-31	Igor Lifshitz	Method for reducing residual alcohols in crystalline valacyclovir hydrochloride
US20050143400A1 (en) *	2003-09-04	2005-06-30	Genny Shamai	Process for preparing famciclovir
US20070112193A1 (en) *	2005-11-14	2007-05-17	Khunt Mayur D	Valacyclovir process

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Beauchamp et al., "Amino acid ester prodrugs of acyclovir", Antiviral Chemistry & Chemotherapy 3(30): 157-164(1992).
Goodman and Gilman's, The Pharmacological Basis of Therapeutics 1193-1198 (9th ed. 1996).
Snyder pp. 549, 552, 571 and 572, Snyder, L.R.; Kirkland, J.J. Introduction to Modern Liquid Chromatography, 2nd ed. (John Wiley & Sons: New York 1979).
Strobel pp. 391-393, 894, 921, 922, 924, 925 and p. 953, Strobel, H.A.; Heineman, W.R., Chemical Instrumentation: A Systematic Approach, 3rd dd. (Wiley & Sons: New York 1989).

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20170052157A1 (en) *	2011-06-01	2017-02-23	Tsumura & Co.	Method of and apparatus for formulating multicomponent drug
US10527595B2 (en) *	2011-06-01	2020-01-07	Tsumura & Co.	Method of and apparatus for formulating multicomponent drug
RU2750867C1 (ru) *	2020-05-18	2021-07-05	Александр Сергеевич Самойлов	Производные гуанина

Also Published As

Publication number	Publication date
CN101068814A (zh)	2007-11-07
CA2578750A1 (fr)	2006-03-16
JP2007513074A (ja)	2007-05-24
KR100890595B1 (ko)	2009-03-25
US20060084668A1 (en)	2006-04-20
IL181548A0 (en)	2007-07-04
WO2006029253A2 (fr)	2006-03-16
EP1692134A2 (fr)	2006-08-23
WO2006029253A3 (fr)	2006-05-26
KR20070046197A (ko)	2007-05-02

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